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题名: Synthesis and cytotoxic activity of novel tetrahydrobenzodifuran-imidazolium salt derivatives
作者: Zhang, Chao-Bo1; Liu, Yang1; Liu, Zheng-Fen1; Duan, Sheng-Zu1; Li, Min-Yan3; Chen, Wen1; null(李艳)2; Zhang, Hong-Bin1; Yang, Xiao-Dong1
刊名: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
关键词: Tetrahydrobenzodifurans ; Imidazolium salts ; Cytotoxic activity ; Cell cycle ; Apoptosis
英文摘要: The synthesis of a series of novel 4-substituted 2,3,6,7-tetrahydrobenzo [1,2-b;4,5-b']difuran-1H-imidazolium salts is presented. The biological properties of the compounds were evaluated in vitro against a panel of human tumor cell lines. Results suggest that the 5,6-dimethyl-benzimidazole or 2-methyl-benzimidazole ring, and substitution of the imidazolyl-3-position with a 2-naphthylmethyl substituent or 2-naphthylacyl substituent, were important to the cytotoxic activity. Notably, 3-(2-Naphthylmethyl)-1-(2,3,6,7-tetrahydrobenzo[1,2-b;4,5-b']difuran-4-y1)methyl)-1H-5,6-dimethyl-benzimidazol-3-ium bromide (42) was found to be the most potent derivative against five human tumor cell lines with 1050 values of 1.06-4.34 mu M and more selective towards SMMC-7721, A549 and SW480 cell lines. 3-(2Naphthylacy1)-1-(2,3,6,7-tetrahydrobenzo[1,2-b;4,5-b']difuran-4-yl)methyl)-1H-2-methyl-benzimidazol- 3-ium bromide (37) showed higher selectivity to SMMC-7721 and MCF-7 cell lines with IC50 values 2.7-fold and 8.4-fold lower than DDP. Study regarding to the antitumor mechanism of action showed that compound 37 could induce cell cycle G1 phase arrest and apoptosis in SMMC-7721 cells. (C) 2017 Elsevier Ltd. All rights reserved.
出版日期: 2017-04-15
卷号: 27, 期号:8, 页码:1808-1814
DOI标识: 10.1016/j.bmc1.2017.02.053
语种: 英语
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内容类型: 期刊论文
URI标识: http://ir.kib.ac.cn/handle/151853/51196
Appears in Collections:植物化学与西部植物资源持续利用国家重点实验室_期刊论文

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作者单位: 1.Yunnan Univ, Key Lab Med Chem Nat Resource, Minist Educ, Kunming 650091, Peoples R China
2.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650204, Peoples R China
3.Univ Penn, Dept Chem, Philadelphia, PA 19104 USA

Recommended Citation:
Zhang, Chao-Bo,Liu, Yang,Liu, Zheng-Fen,et al. Synthesis and cytotoxic activity of novel tetrahydrobenzodifuran-imidazolium salt derivatives[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,2017,27(8):1808-1814.
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